


Knee High

by kittenofdoomage



Series: SPN Kink Bingo [6]
Category: Supernatural
Genre: Anal, Brothers, Incest, M/M, SPN Kink Bingo, Sex, Shoe Kink, Smut, Wincest - Freeform, high heel boots, stripper boots, unprotected sex
Language: English
Status: Completed
Published: 2016-10-03
Updated: 2016-10-03
Packaged: 2018-08-19 10:14:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,191
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8201569
Author URL: https://archiveofourown.org/users/kittenofdoomage/pseuds/kittenofdoomage
Summary: It’s porn, of the Wincest variety, where Dean discovers his fetish for Sam in heels, even if he doesn’t need the extra inches. Set circa season three. Filling a square for @spnkinkbingo.Square filled: Shoe Kink





	

 

‘Sam, what are these?’

The younger Winchester looked up, raising an eyebrow before blushing bright red at the two objects dangling from his big brother’s hand. Words stuck in his throat as Dean stood straight, a smirk pulling at the corner of the elder’s lips.

‘Leather and laces, baby brother.’ Dean held the boots up a little higher, running his finger around the pointed toe. ‘How the hell did you find hooker boots big enough to fit your gigantor feet?’

Sam looked down at his hands as he stood up from the bed, not making a move to snatch the boots from Dean’s iron grip. ‘A lady in Kentucky. She, er, she does custom orders. When we were working that case, with the poltergeist, I stopped in and…’

Dean gave a low whistle, holding the boots out. ‘Gotta say, Sammy...I’ve always liked boots on a lady,’ Sam tried to ignore the thread of jealousy that burned as it ran through his gut, ‘but I never thought I’d wanna see you dressed up in some heels.’ He stretched his arm, and Sam took the boots gently, letting them hang from his fingers as he contemplated Dean’s words, not expecting what his brother would ask of him next.

‘Put them on.’

His throat felt thick as he swallowed, raising his eyes slowly to meet his brother’s green gaze. The pupil in Dean’s eyes was blown, black as night, lust practically vibrating off of him as he waited for Sam’s response.

Sam’s chest expanded as he sucked in a breath, backing away from his brother towards the bathroom, as Dean watched him go, not saying anything in the face of Sam’s retreat.

Once the bathroom door was shut, Sam leaned against the wood, shutting his eyes and expelling the breath he’d taken. The boots felt hot in his shaking fingers, and after a few seconds of listening to his heart race, he opened his eyes, looking down at them.

He’d never intended for Dean to find his secret, but now that it was out in the open, he felt a wave of relief. After he’d bought them from the very nice lady, who’d made a lot of shoes for drag queens and didn’t question his order at all, he’d only worn them once or twice, mostly when he was alone. Once, he’d put them on when Dean was asleep, and wondered what his brother would think if he woke up.

The boots made a thunk as they hit the lid of the toilet, and Sam stared at them for a second or two, before looking up to the mirror. His reflection looked back at him, mocking him with flushed skin, and his palm covered the bulge in his pants as he heard Dean groan from the other room.

Fuck, this was wrong. It had always been wrong, the things him and Dean did in the dark...but this...this…

His fingers pulled at the button of his jeans, releasing the pressure against his dick, and he looked down, grunting a little at how fucking hard he was. His eyes flickered to the boots again, and his teeth grabbed his bottom lip as he contemplated the options. He could ignore this, and hope Dean didn’t bring it up again, or…

Before he realised what he was doing, his hands were pushing his pants down his legs, simultaneously toeing his shoes off and kicking them against the bath. The jeans landed in a pile on top of the ratty old Timberlands, and his socks followed. He pulled his shirt over his head, dropping it haphazardly against the rest of his clothing, before removing his boxer briefs.

No going back now.

*****

Dean threw himself on the bed as Sam shut the bathroom door, sighing heavily and instantly reaching for the aching boner straining at his jeans. The second he’d found those boots, his overactive imagination had his little brother stood in them, looking awkward and fucking sexy all in one hit.

His hand closed around his dick and he arched his back on the bed, groaning loudly as he started to move his fingers, massaging himself slowly. He could hear Sam moving around in the bathroom, and god, Dean wished he’d come out here.

The ache only increased as he touched himself with his eyes closed, using his free hand to push his jeans further down his legs. His mind was conjuring all sorts of images of Sam, dressed up in those boots, laced up to the knees, maybe with some panties on, soft girlish fabric. Another groan left his lips as he made the image work, and he barely heard the bathroom door open.

‘Dean?’

His eyes snapped open and he looked towards the bathroom, his jaw dropping as he saw his brother filling up the doorway. He was completely naked, hard and leaking as his eyes met Dean’s shyly, stepping out into the room. The boots on his feet clicked as they hit the metal trim of the carpet, and Dean pushed up, still holding onto his dick as he watched Sam walk a little further into the room, slightly unsteady on his feet.

‘Fuck, baby brother,’ he hissed, unable to tear his eyes away. ‘You have any idea how hot you look in those boots?’

Sam smiled, blushing bright red  _ everywhere _ , and his cock jumped at the compliment. ‘I don’t...fuck, Dee, I don’t even know what I’m doing.’

‘Working it, baby,’ Dean smirked widely, scooting himself down the bed. ‘How about you turn around and show me that fine ass in those boots.’ Sam hesitated, almost like he was going to bolt, and Dean reached out. ‘Sam, trust me, sweetheart, you look...hotter than anything I’ve ever seen.’ His fingers just about grazed Sam’s thigh, and the younger man shivered, moving closer without even thinking about it. ‘You got me so fucking hard, Sammy, you see this?’ Hazel eyes met his, before drifting down to Dean’s thick cock, which twitched in his grasp.

‘I see, Dee,’ Sam whispered, dropping to his knees in the threadbare motel carpet. The boots stuck out behind him, and Dean groaned as his little brother peeled his fingers away from his dick, replacing them with his own. He leaned back on his arms as Sam watched him, jerking his cock slowly. ‘You like the boots?’

‘Fuck, I do.’ Dean replied, his voice trembling as he spoke. ‘Just like that, Sammy, shit -’ His words cut off as he moaned his brother’s name, and Sam smiled coyly, keeping his eyes on his brother through thick lashes, his fingers tightening around the tip of his cock.

‘Wanna see me ride you wearing these, Dee? Or you want me bent over the bed?’ Sam bent his head, lapping at the tip of Dean’s cock, and his brother gave a sinful noise. ‘Gonna suck your dick so good, Dee. Just like you like.’

His lips slid down over his brother’s length, swirling his tongue around the tip and he could barely keep the smile off his face as Dean’s hand threaded through his hair, holding him tightly as he started to fuck Dean with his mouth. ‘Fucking perfect, baby brother, so good for me, little cockslut. God, don’t stop, don’t...shit, Sammy.’

Sam closed his eyes, focusing on the feelings circling in his gut, the rough drag of his own hard cock against the comforter, and he knew the fabric would be wet with his need. Saliva ran over Dean’s balls as Sam sucked his cock with vigor, his fingers tight around the base as he bobbed his head. Dean’s fingers remained in his hair, not guiding his movements or forcing them, just simply holding.

The taste of his brother’s precome on his tongue made him pull away, and he panted as he looked up, seeing Dean looking back at him, flushed and breathing heavily. A brief second of eye contact and Dean was dragging Sam to him in a heated kiss, tasting himself on his lips, moaning into his mouth as his fingers pushed at his pants.

‘On the bed, Sammy, spread those sweet legs for me.’ Sam nodded, crawling onto the bed, laying on his stomach until Dean tutted and he looked up at him in confusion. ‘Na-uh. On your back, baby boy.’

‘Dee?’

Dean smiled, shucking his jeans off, his shirt quickly following suit as Sam turned on the bed, pulling his knees up a little, the heels of the hooker boots digging into the mattress. His cock bounced on his stomach as he watched Dean approach him, the leer on his brother’s face making warmth pool in his belly.

‘You have any idea…’ Dean growled, kneeling between his brother’s legs, his hands running over his thighs. ‘Fuck, Sammy, look at you.’ He pushed Sam’s thighs up, raising his feet off of the bed, and the elder groaned as Sam’s neck arched. His hole clenched as Dean spread his thighs wide, almost to the point of discomfort.

The lube was in the bedside table, and Dean grunted in annoyance as he realised he was going to have to release his hold on Sam to grab it. As he relinquished his hold, Sam whimpered in need, the whimper turning into a mewl when Dean’s body pressed against his as he reached for the lube in the drawer. 

Leaning back, Dean kept his eyes on Sam, squeezing a generous amount onto his fingers before dropping his hand to Sam’s ass, trying to reign in the urgency in his touch as Sam wiggled underneath him.

‘Dee -’

‘I know, baby boy, I know what you need.’ Dean groaned in tandem with his brother as he eased two fingers into his twitching hole, scissoring them gently. Sam whined loudly, pushing his ass down, desperate for more, and Dean smiled, shaking his head. ‘You need to relax, Sammy. You know I’m not gonna just rail you like that.’

‘I know,’ Sam panted, his fingers clutching at the bed covers. ‘I just...need you, Dee. Need you inside me.’

Dean groaned. ‘Can’t talk like that, sweetheart. I’m gonna lose my cool.’

Sam’s smile was barely a secret. ‘Please,  _ Dean _ , fuck me. Wanna feel you in me, filling me up.’ The fingers in his ass gave a harder thrust, and the younger Winchester whined in need, his legs jerking, heels digging into the bed. ‘ _ Dee  _ -’

The fingers left him, and he mewled again, raising his ass, hearing Dean flick the lid of the lube again. ‘I got you, Sammy, I got you.’ Sam arched as he felt Dean’s slicked up cock press against his hole. ‘I got you.’

Sam gasped in pleasure, his hands blindly reaching for Dean as he sank into him, not stopping until he was bottomed out, his pelvis flush with Sam’s ass. His long fingers curled around Dean’s biceps, just as Dean’s mouth pressed against his, the elder’s hands running down the underside of his thighs to the boots.

‘Fucking hot as hell, Sam. Dressed up for me like a whore.’ Sam whimpered at Dean’s words, feeling him tug at the boots. ‘Think you’d put on some sexy panties for me too, baby boy?’ He grunted, moving his hips again, pulling out of Sam a little way before pushing back in, his cock twitching and throbbing in the heat that encased him. ‘Always so fucking tight for me, huh?’

‘Dee, I’m gonna come, I can’t -’

‘Don’t hold back for me, Sammy,’ Dean grinned, not stopping in his movements as Sam’s cock pulsed, trapped between their bodies. ‘Come on, baby, come all over yourself.’

Sam whined, pushing back against Dean, urging him on as he clung to him. His pants and mewls only made Dean harder, and a few moments later, there was warmth and wet between them, Sam’s come splattering over his chest and Dean’s.

‘That’s it, sweetheart.’ Dean’s fingers tightened around the boots as his orgasm built low in his belly, and he grunted as he fucked Sam harder into the mattress. Sam’s fingers pressed crescent shaped nail marks into his biceps, the boots squeaked as Dean held onto them. ‘Gonna come, Sammy, gonna fill you up, yeah?’ Sam nodded, breathing heavily.

Dean’s orgasm slammed into him and he held himself against Sam, letting rope after rope of come fill his brother to the brim, spilling out around his cock as Sam whined and bucked underneath him. They collapsed together, sharing lazy, slow kisses, until Dean withdrew, soft and spent.

Sam watched Dean move around the room, grabbing wipes to clean up the mess he’d made. He flexed his feet in the boots, feeling the pleasant warmth in his ass that always followed the intense coupling between them.

‘So, I should wear panties next time?’ Sam purred, and Dean looked up, a smile spreading over his face. ‘If it gets you that hot, I mean…’ The elder Winchester chuckled, abandoning his quest to clean up, and sliding beside Sam on the bed, swallowing down any further words with a hot kiss.

Maybe they were both going to hell. But Sam knew that he’d at least be strutting it in his hooker boots.


End file.
